In the preparation of perfumed and odorant compositions, exemplified by perfumes and other perfumed compositions such as soaps and detergent compositions, cosmetics of various kinds such as creams, lotions, etc., it has long been known to utilize various alkyl cyclopentenones, alkyl cyclopentenone derivatives, alkyl cyclopentanones or alkyl cyclopentanone derivatives to impart certain fatty-floral odors to such perfumed and odorant compositions. Such alkyl cyclopentenones and alkyl cyclopentenone derivatives or the corresponding cyclopentanones are known to art and are associated by those skilled in the art with jasmin or jasmin-like odors and have been and are used for imparting jasmin or jasmin-like odors to perfumes and other perfumed or odorant compositions in which said alkyl cyclopentenones and alkyl cyclopentenone derivatives are incorporated. Illustrative of such alkyl cyclopentanones and derivatives thereof are methyl jasmonate and methyl hydrojasmonate (or methyl dihydrojasmonate) which possess strong jasmin odors. Methyl jasmonate, for instance, has been found to be an important odoriferous constituent of Jasmin oil and, in addition to being found to be present in Jasmin oil, its structure has been established and it, as well as numbers of other alkyl cyclopentenones and derivatives thereof, have been synthesized including the aforesaid methyl dihydrojasmonate; cis-Jasmone (3-methyl-2-(cis-2-penten-1-yl)-2-cyclopenten-1-one); amyl cyclopentenone (2-n-amyl-cyclopenten-2-one-1); etc. All of the aforesaid alkyl cyclopentenones, for instance, though varying somewhat in their jasmin odor, have the common property or characteristic, as noted above, of possessing a jasmin or jasmin-like odor, or imparting jasmin notes to perfumes and other odorant compositions in which said alkyl cyclopentenones or alkyl cyclopentanones are incorporated. Illustrative literature in support of the foregoing statements are such publications as Perfume and Flavor Chemicals, Vol. I, by Steffen Arctander, published by the Author, 1969, Section 108: Amyl Cyclopentanone; Section 1786: cis-Jasmone; and Section 1789: iso-Jasone; and Vol. II by the same Author, published in 1969, Section 2076: Methyl Hydrojasmonate. As noted above, alkyl cyclopentenones and alkyl cyclopentanones generally have fatty-floral odors, and, while such odors are variable, so far as is known the odors of the alkyl cyclopentenones and alkyl cyclopentanones have universally been recognized to be of distinctly jasmin character. Illustrative examples of other alkyl cyclopentenones and alkyl cyclopentanones which have been produced, to wit, those having the following formulae: ##STR1## are likewise characterized by a jasmin odor.
In Bull. Soc. Chim. France, 1963(6), pp. 1210-1213, the authors, Lenfant et al, point out, with respect to methyl jasmonate, referred to above (and also referred to in Bedoukian, Amer. Perf. & Cos., Vol. 79 (1964), pp. 27-37), that it is an important ingredient or odoriferous constituent of Jasmin flower oil, and that Demole and collaborators have previously established the structure of methyl jasmonate and have effected the synthesis thereof as well as that of methyl dihydrojasmonate. Lenfant et al, in their aforesaid article, which article is also referred to in footnote 73 on p. 36 of said Bedoukian article, undertake, as an alleged interesting project, the effecting of the synthesis of certain compounds related to methyl dihydrojasmonate and to methyl jasmonate with the objective of studying the relationships which exist between structure and olfactive properties of said certain compounds. The work which they report in their aforesaid article describes the synthesis of three compounds, denoted by Roman numerals (IV), (XVIb) and (XXb), namely:
(IV). (n-amyl-2-oxo-3-cyclopentyl)-acetone, which may also be denoted as [2-(n-amyl)-3-oxocyclopentyl]-acetone. PA1 (XVIb). methyl (n-amyl-3-oxo-4-cyclopentyl)-acetate, which also may be denoted as methyl [3-(n-amyl-4-oxocyclopentyl]-acetate. PA1 (XXb). (n-amyl-2-carbomethoxymethyl-.gamma.-butanolide, which also may be denoted as 2-n-amyl-carbomethoxymethyl-.gamma.-butanolide.
Of these three compounds, compound IV, namely (n-amyl-2-oxo-3-cyclopentyl)-acetone is another chemical designation for the aforementioned compound 2-n-pentyl-3-(2-oxopropyl)-1-cyclopentanone with which the present invention is concerned.
Although, as noted above, the Lenfant et al article purports to deal with a study of the relationships which exist between structure and olfactive properties of the aforesaid compounds (IV), (XVIb) and (XXb), said article proper makes no reference whatever to the odor of compound (IV) nor, for that matter, to the odor of compounds (XVIb) and (XXb), nor to any utility or possible utility of any of said three compounds. All that is disclosed as to said compounds are the particular procedures utilized for the syntheses thereof, certain analyses of the compounds, and measurements of certain of their physical properties. Since, as noted above, alkyl cyclopentenone and cyclopentanone derivatives, in general and as exemplified by methyl jasmonate and methyl dihydrojasmonate, have long been known to possess a jasmin or jasmin-like odor, it could perhaps have been assumed or expected that the aforementioned compounds (IV), (XVIb) and (XXb) of said Lenfant et al article would, therefore, possess a jasmin or jasmin-like odor. However, as noted above, nothing whatever is stated in said article concerning any odors of said compounds nor any utility or possible utility of any of said three compounds.
In the preparation of the compound (IV) in accordance with the experimental part of said Lenfant et al article at pp. 1212-1213, a complex process is specifically described involving what amounts to a 7-stage process which may be shown in outline form as follows: ##STR2##
When said 7-stage process described by Lenfant et al for the production of compound (IV) is carried out, it has been found, by actual experimental work which carefully duplicated the aforesaid Lenfant et al procedure described on pp. 1212-1213 for the synthesis of compound (IV), the said compound (IV), even when separated and purified by adsorption chromatography, and fundamentally satisfying the infrared spectrum (showing two carbonyl bands) at 1736 cm.sup.-1 (cyclopentanone) and at 1718 cm.sup.-1 (aliphatic ketone), is not only characterized by an odor which differs substantially from the 2-n-pentyl-3-(2-oxopropyl)-1-cyclopentanone which is utilized in accordance with the process of the present invention (even at similar purity levels evidenced by essentially identical gas chromatograms as established by gas phase chromatography), but, further, the aforesaid Lenfant et al compound (IV), as prepared as described by Lenfant et al in their 7-stage process, is characterized by a garlicky odor which renders it unusable and of no value in perfumery. Hence, wholly apart from other aspects of the Lenfant et al article in relation to the invention of the present application, a matter which is discussed in further detail below, the garlicky odor of even a substantially purified compound (IV), made as specifically described by the said Lenfant et al 7-stage process, makes the compound, for all practical purposes, worthless for use as an ingredient for producing perfumed compositions. In short, while the Lenfant et al article discloses a synthesis for the preparation of what actually results, even after substantial purification treatment, in a garlicky-odor-bearing 2-n-pentyl-3-(2-oxo-propyl)-1-cyclopentanone, said article is devoid of any concept, suggestion or teaching of the present invention which involves perfumed compositions which contain a carrier which may, for instance, be a perfume, or a solid or liquid detergent, or a synthetic washing agent, or an aerosol, or a cosmetic of any kind, up to about 20%, preferably 1 to 20%, by weight of the compositions, of a 2-n-pentyl-3-(2-oxo-propyl)-1-cyclopentanone which is free from a garlicky odor, to impart a magnolia odor to the compositions, nor other features of the present invention as pointed out below.